Surprisingly long-lived ascorbyl radicals in acetonitrile: Concerted proton-electron transfer reactions and thermochemistry

Journal of the American Chemical Society

Volumn 130, Issue 24, 2008, Pages 7546-7547

  Warren, Jeffrey J ^a   Mayer, James M ^a  

^a UNIVERSITY OF WASHINGTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; ASCORBIC ACID DERIVATIVE; HYDROGEN; OXYGEN; PROTON; RADICAL;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION KINETICS; CYCLIC POTENTIOMETRY; DISSOCIATION; ELECTROCHEMISTRY; ELECTRON; ELECTRON SPIN RESONANCE; ELECTROSPRAY MASS SPECTROMETRY; ENTHALPY; HYDROGEN BOND; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; SPECTROPHOTOMETRY; ULTRAVIOLET SPECTROSCOPY;

ACETONITRILES; ASCORBIC ACID; ELECTRON TRANSPORT; FREE RADICALS; HEAT; OXIDATION-REDUCTION; PROTONS; SOLVENTS; TEMPERATURE;

EID: 45249086311     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja802055t     Document Type: Article

References (39)

1. (a) Vitamin C in Health and Disease; Packer, L., Fuchs, J., Eds.; Marcel Dekker: New York, 1997; Vol. 5.
2. (b) Davies, M. B.; Austin, J.; Partridge, D. A. Vitamin C Its Chemistry and Biochemistry; The Royal Society of Chemistry: Cambridge, 1991.
3. (c) Bielski, B. H. J. In Ascorbic Acid: Chemistry, Metabolism, and Uses; Seib, P. A., Tolbert, B. M. Eds.; Advances in Chemistry Series 200; American Chemical Society: Washington, D.C., 1982; pp 81-100.
4. -4 M), unless otherwise noted.
5. (a) Huynh, M. H. V.; Meyer, T. J. Chem. Rev. 2007, 107, 5004-5064.
6. (b) Mayer, J. M. Annu. Rev. Phys. Chem. 2004, 55, 363-390.
7. (a) Njus, D.; Wigle, M.; Kelley, P. M.; Kipp, B. H.; Schlegel, H. B. Biochemistry 2001, 40, 11905-11911.
8. (b) Vuina, D.; Pilepi, V.; Ljubas, D.; Sankovi, K.; Sajenko, I.; Uric, S. Tetrahedron Lett. 2007, 48, 3633-3637.
9. (c) Biondi, C.; Galeazzi, R.; Littarru, G.; Greci, L. Free Radical Res. 2002, 36, 399-404.
10. (a) Bisby, R. H.; Parker, A. W. Arch. Biochem. Biophys. 1995, 317, 170-178.
11. (b) Njus, D.; Kelley, P. M. FEBS Lett. 1991, 284, 147-151.
12. (a) Mayer, J. M.; Hrovat, D. A.; Thomas, J. L.; Borden, W. T. J. Am. Chem. Soc. 2002, 124, 11142-11147.
13. (b) Litwinienko, G.; Ingold, K. U. Acc. Chem. Res. 2007, 40, 222-230.
14. (c) Costentin, C.; Evans, D. H.; Robert, M.; Savéant, J.-M.; Singh, P. S. J. Am. Chem. Soc. 2005, 127, 12490-12491.
15. Manner, V. W.; Markle, T. F.; Freudenthal, J.; Roth, J. P.; Mayer, J. M. Chem. Commun. 2008, 256-258.
16. (a) Wittine, K.; Gazivoda, T.; Marku, M.; Mrvo-Sermek, D.; Hergol-Brundi, A.; Cetine, M.; Ziher, D.; Gabelica, V.; Mintas, M.; Rai-Mali, S. J. Mol. Struct. 2004, 687, 101-106.
17. (b) Olabisi, A. O.; Wimalasena, K. J. Org. Chem. 2004, 69, 7026-7032.
18. (c) Zhang, L.; Lay, P. A. J. Am. Chem. Soc. 1996, 118, 12624-12637.
19. (d) Warren, J. J.; Mayer, J. M. J. Am. Chem. Soc. 2008, 130, 2774-2776.
20. Full details are given in the Supporting Information.
21. Schuler, R. H. Radiat. Res. 1977, 69, 417-433.
22. Ohmori, M.; Takagi, M. Agric. Biol. Chem. 1978, 42, 173-174.
23. Cioffi, N.; Losito, I.; Terzano, R.; Zambonin, C. G. Analyst 2000, 125, 2244-2248.
24. Kirino, Y. Chem. Lett. 1974, 3, 153-158.
25. Bielski, B. H. J.; Allen, A. O.; Schwarz, H. A. J. Am. Chem. Soc. 1981, 103, 3516-3518.
26. 9
27. Paleos, C. M.; Dais, P. J. Chem. Soc., Chem. Commun. 1977, 345-346.
28. Isutzu, K. Acid-Base Dissociation Constants in Dipolar Aprotic Solvents; Blackwell Scientific: Oxford, 1990.
29. Kaljurand, I.; Kütt, A.; Soovälti, L.; Rodima, T.; Mäemets, V.; Leito, I.; Koppel, I. A. J. Org. Chem. 2005, 70, 1019-1028.
30. 2 in acetonitrile.
31. (a) Tilset, M. Electron Transfer in Chemistry; Balzani, V., Ed.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 2, pp 677-713.
32. (b) Mader, E. A.; Davidson, E. R.; Mayer, J. M. J. Am. Chem. Soc. 2007, 129, 5153-5166.
33. (a) Mader, E. A. Ph.D. Thesis, University of Washington, Seattle, WA, 2007.
34. (b) Mader, E. A.; Manner, V. W.; Wu, A.; Mayer, J. M. Manuscript in preparation.
35. (c) See Supporting Information.
36. (a) Williams, N. H.; Yandell, J. K. Aust. J. Chem. 1982, 35, 1133-1144.
37. (b) Creutz, C. Inorg. Chem. 1981, 20, 4449-4452.
38. Mulder, P.; Korth, H.-G.; Pratt, D. A.; DiLabio, G. A.; Valgimigli, L.; Pedulli, G. F.; Ingold, K. U. J. Phys. Chem. A 2005, 109, 2647-2655.
39. 9